Ball Don’t Five: Top 5 worst contracts in the NBA moving forward

As we continue to work our way through the endless summer between the Finals and Opening Night, we’ll pause each Friday to briefly consider and count down some NBA-related topic of note. We like starting lineups and round numbers, so we’ll run through a handful of items each week. With a nod to our friends at Dr. Saturday, welcome to Ball Don’t Five. 

This week’s installment: The NBA’s five worst contracts moving forward.

Thanks to advanced metrics and NBA teams now employing people who actually grasp the salary cap, there are fewer and fewer horrible contracts each July. The $20 million cap expansion in 2016 will also make some of the current albatrosses more palatable when Hassan Whiteside signs for $100 million next summer. 

As long as the New York Knicks remain an NBA franchise, however, there will still be horrendous financial decisions made every year. As we retire the expiring contracts of Joe Johnson (6 years, $123.7 million), Kobe Bryant (2 years, $48.5 million), Nene (5 years, $65 million), Roy Hibbert (4 years, $58.4 million) and Eric Gordon (4 years, $58.4 million) this season — and with respect to every crazy deal the Cavaliers have signed this summer — let’s examine the league’s five worst deals going forward.

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5. Wesley Matthews, Dallas Mavericks. Even when healthy, Matthews may not have been worth four years and $70 million this summer. A prolific 3-point shooter and shutdown defender on the wing, he was a fantastic third option for the Trail Blazers and the glue that held a 50-win team together for the past two seasons.

But is that worth $17.5 million a season? Mavs owner Mark Cuban certainly thought so, hoping Matthews would fill a similar role alongside Chandler Parsons, Dirk Nowitzki and DeAndre Jordan. But once Jordan reneged on his deal, you wonder if Cuban wishes he could’ve done the same with Matthews in the aftermath. After all, Matthews generously estimated his own annual value at $15 million weeks earlier.

And we haven’t even mentioned Matthews’ ruptured Achilles tendon, requiring season-ending surgery from which NBA players rarely — if ever — regain form.

Omer Asik, New Orleans Pelicans. On the surface, signing Asik to a five-year, $60 million deal this summer to coincide with Anthony Davis’ extension should’ve shored up the Pelicans’ frontcourt for the foreseeable future. Lineups featuring that duo allowed 100.6 points per 100 possessions in 2014-15 — a mark that would rank as the league’s seventh-best defensive rating if extrapolated over a full season.

Except, Asik is so severely limited on offense that he hurt the Pelicans more on that end than he helped them defensively, as his negative real plus-minus reflected last season. In their first-round series against the Warriors, the two most common lineups featuring Asik were outscored by 18.4 and 26.3 points per 100 possessions, respectively, because Golden State ignored him in favor of double-teaming Davis.

That’s a problem for a franchise that hopes to build a contender around Davis. The Pelicans fared far better with Davis manning the middle alongside stretch four Ryan Anderson, and 7-footer Alexis Ajinca — signed to a more affordable four-year, $20.2 million extension — has proven capable of approximating Asik’s production in more traditional lineups. In other words, why commit to Asik for so much and for so long?

Reggie Jackson, Detroit Pistons. What do you do when your inefficient starting point guard tears his Achilles before entering the final year of his contract? Why, you offer twice as much money to an even more inefficient point guard, of course.

Brandon Jennings was finally coming into his own on the Pistons. His turnovers were down, his shooting percentages were up, and the result was the best on/off rating of his six-year career. And then the tendon in his left ankle ruptured. With it went the playoff prayers of a team that had won 12 of 15 following a 5-23 start. Meanwhile, two of the three players Detroit traded for Jennings two years earlier — Brandon Knight and Khris Middleton — were keeping Milwaukee in contention.

And then Stan Van Gundy got weird. In two separate deals on deadline day, the Pistons coach and president traded a trio of inexpensive and impactful role players — D.J. Augustin, Kyle Singler and Jonas Jerebko — along with a pair of second-round picks for Jackson and Tayshaun Prince. The acquisition of Prince’s additional salary made absolutely no sense, and Jackson’s arrival might make less, if that’s possible.

Jackson posted impressive per-minute traditional statistics off the bench in Oklahoma City, although he required a high usage rate and a ton of shots to get those numbers. He also fell out of favor on the Thunder after vocalizing his desire for a starting role and big contract elsewhere, and that doesn’t always sit well, especially on a roster that could compete for a championship when healthy.

It’s his right to seek more minutes and money, even if it’s on a team battling from the middle of a muddled Eastern Conference. Over the final month of last season, Jackson posted numbers (19.9 points, 10.9 assists and 4.9 rebounds while shooting nearly 40 percent from 3-point range) worthy of his five-year, $80 million deal.

But paying a $16 million salary to someone who spent three-plus season proving himself as an individualistic and inefficient talent rarely translates into winning basketball. The fact Knight and Middleton each signed through 2020 for $10 million less will only make matters when Detroit fans watch Jennings come off the bench.

Enes Kanter, Oklahoma City Thunder. Sam Presti had to do it. With Kevin Durant’s free agency looming over the franchise, the OKC general manager couldn’t part with another player over a price tag, even if matching Portland’s four-year, $70 million contract offer to Kanter meant spending $10 million more than it would’ve cost to keep James Harden in a Thunder uniform only a few years earlier.

Presti had to show Durant the team was willing to exceed the luxury tax in order to appease the former MVP’s fears that the organization would never spend enough to build a title contender around him, even if it meant handicapping the roster with one of the league’s worst defensive centers at a rate of $17.5 million per season.

Of the 11 Thunder lineups that played at least 50 minutes together in 2014-15, Kanter appeared on four of them, and all but one was outscored by at least 7.4 points per 100 possessions. Despite the Swiss center’s obvious talent as a low-post scorer and rebounder, Oklahoma City features more impactful options in the middle of both small-ball combinations (Serge Ibaka) and bigger lineups (Steven Adams).

While OKC needed Kanter from an image standpoint, the Thunder don’t require his services to win this season, which will be the real key to keeping Durant down the line. Kanter’s presence might actually hinder Oklahoma City’s efforts on the court in 2015-16, and his cumbersome contract could prevent them from improving in the future, especially since his salary skyrockets 15 percent if he’s ever traded. Ouch.

Carmelo Anthony, New York Knicks. Don’t get me wrong. As a proud former Syracuse student, I love me some Melo. He’s an extraordinary offensive talent who has led the league in scoring and shot 40 percent from 3-point range despite being every defense’s sole focus in his last two healthy seasons, but he’s also a black hole whose hero ball can extinguish the bright lights of basketball in New York City.

In the summer of 2014, the Knicks were entering another rebuilding project with the same finish date as every previous renovation since 1973: someday. With that in mind, the new brass acted just as the old brass would, signing a 30-year-old Anthony to a five-year, $124.1 million contract — the NBA’s richest deal at the time.

Making matters worse, Anthony had been dealing with knee problems in the months leading up to that contract, and then missed the entirety of the second half of his first year making $22.5 million due to, you guessed it, season-ending knee surgery.

His salary is set to increase each of the next four seasons, at which point he’ll be 35. Robin Lopez and rookie Kristaps Porzingis are also signed through 2019 for a combined $17-20 million per season, which makes for a strange triumvirate taking up half your salary cap, if the goal is to win a championship. But the real motivation behind signing Anthony probably had more to do with selling tickets in Madison Square Garden now than building toward a title, in which case — #knickstape?

Previously on Ball Don’t Five:

• Top 5 players who have never been to the playoffs
• Top 5 teams with 5 or fewer national TV games
• Top 5 great teams that never won a title
• Top 5 players facing a make-or-break season
• Top 5 retired players who never made an All-Star team
• Top 5 coaches who aren’t in the Hall of Fame

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Ben Rohrbach is a contributor for Ball Don’t Lie and Shutdown Corner on Yahoo Sports. Have a tip? Email him at [email protected] or follow him on Twitter! Follow @brohrbach